CA3015309C - Composes de carbapeneme - Google Patents
Composes de carbapeneme Download PDFInfo
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- CA3015309C CA3015309C CA3015309A CA3015309A CA3015309C CA 3015309 C CA3015309 C CA 3015309C CA 3015309 A CA3015309 A CA 3015309A CA 3015309 A CA3015309 A CA 3015309A CA 3015309 C CA3015309 C CA 3015309C
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- f2hc
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- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 241
- 150000003839 salts Chemical class 0.000 claims abstract description 136
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 37
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 24
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 23
- 239000003814 drug Substances 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 386
- -1 cyano, carbamoyl Chemical group 0.000 claims description 130
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 229910052757 nitrogen Inorganic materials 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 56
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 53
- 125000004122 cyclic group Chemical group 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 239000011734 sodium Substances 0.000 claims description 21
- 125000002619 bicyclic group Chemical group 0.000 claims description 20
- 125000006413 ring segment Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 125000004193 piperazinyl group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000002393 azetidinyl group Chemical group 0.000 claims description 11
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 11
- AQIAIZBHFAKICS-UHFFFAOYSA-N methylaminomethyl Chemical compound [CH2]NC AQIAIZBHFAKICS-UHFFFAOYSA-N 0.000 claims description 11
- 150000003536 tetrazoles Chemical class 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 150000003852 triazoles Chemical class 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052731 fluorine Chemical class 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000003003 spiro group Chemical group 0.000 claims description 6
- UWQVPLPJLRBXRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,2-c]pyridine Chemical group C1NCCC2NCCC21 UWQVPLPJLRBXRH-UHFFFAOYSA-N 0.000 claims description 5
- 241000588722 Escherichia Species 0.000 claims description 5
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 5
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 5
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 241000588923 Citrobacter Species 0.000 claims description 4
- 241000588914 Enterobacter Species 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 150000002460 imidazoles Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- UZHVXJZEHGSWQV-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole Chemical group C1NCC2CCCC21 UZHVXJZEHGSWQV-UHFFFAOYSA-N 0.000 claims description 3
- YETODIXQMRZKEG-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[2,3-c]pyrrole Chemical group C1NCC2NCCC21 YETODIXQMRZKEG-UHFFFAOYSA-N 0.000 claims description 3
- AKYVCAZZLJAUMA-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,6-naphthyridine Chemical compound C1CNCC2CCCNC21 AKYVCAZZLJAUMA-UHFFFAOYSA-N 0.000 claims description 3
- NHJZLTUVYSLGRQ-UHFFFAOYSA-N 1,7-diazaspiro[3.5]nonane Chemical compound N1CCC11CCNCC1 NHJZLTUVYSLGRQ-UHFFFAOYSA-N 0.000 claims description 3
- RHRMCNWRSJMIFI-UHFFFAOYSA-N 1,9-diazaspiro[4.5]decane Chemical compound C1CCNC21CNCCC2 RHRMCNWRSJMIFI-UHFFFAOYSA-N 0.000 claims description 3
- 241000589291 Acinetobacter Species 0.000 claims description 3
- 241000588748 Klebsiella Species 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 3
- 241000588771 Morganella <proteobacterium> Species 0.000 claims description 3
- 241000607720 Serratia Species 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- JMWPSCUIQIMVQH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,4-c]pyridine Chemical group C1NCCC2CNCC21 JMWPSCUIQIMVQH-UHFFFAOYSA-N 0.000 claims description 2
- PZJFUNZDCRKXPZ-UHFFFAOYSA-N 2,5-dihydro-1h-tetrazole Chemical compound C1NNN=N1 PZJFUNZDCRKXPZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000005959 diazepanyl group Chemical group 0.000 claims description 2
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 150000003235 pyrrolidines Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 63
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- JFIOVJDNOJYLKP-UHFFFAOYSA-N bithionol Chemical compound OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O JFIOVJDNOJYLKP-UHFFFAOYSA-N 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- QFCMBRXRVQRSSF-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole Chemical group C1NCC2CNCC21 QFCMBRXRVQRSSF-UHFFFAOYSA-N 0.000 claims 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 2
- BFAHRLVWYDSXIA-UHFFFAOYSA-N 1,8-diazaspiro[4.5]decane Chemical compound C1CCNC21CCNCC2 BFAHRLVWYDSXIA-UHFFFAOYSA-N 0.000 claims 2
- XLTAYZVSYHTRHI-UHFFFAOYSA-N 1,9-diazaspiro[5.5]undecane Chemical compound N1CCCCC11CCNCC1 XLTAYZVSYHTRHI-UHFFFAOYSA-N 0.000 claims 2
- LATHDVDCFBYVBB-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[2,3-c]pyridine Chemical compound C1CNCC2NCCC21 LATHDVDCFBYVBB-UHFFFAOYSA-N 0.000 claims 2
- IJVGODUTGYOVKR-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,2-b]pyridine Chemical compound N1CCCC2NCCC21 IJVGODUTGYOVKR-UHFFFAOYSA-N 0.000 claims 2
- KSCPLKVBWDOSAI-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical group N1CCCC2CNCC21 KSCPLKVBWDOSAI-UHFFFAOYSA-N 0.000 claims 2
- OXPIFHNJGOJJQZ-UHFFFAOYSA-N 2,7-diazaspiro[3.4]octane Chemical compound C1NCC11CNCC1 OXPIFHNJGOJJQZ-UHFFFAOYSA-N 0.000 claims 2
- DROZYMFJWSYDRY-UHFFFAOYSA-N 2,7-diazaspiro[3.5]nonane Chemical compound C1NCC11CCNCC1 DROZYMFJWSYDRY-UHFFFAOYSA-N 0.000 claims 2
- DDVRNOMZDQTUNS-UHFFFAOYSA-N 2,7-diazaspiro[4.4]nonane Chemical compound C1NCCC11CNCC1 DDVRNOMZDQTUNS-UHFFFAOYSA-N 0.000 claims 2
- WYZZNMWIWHRXRM-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decane Chemical compound C1NCCC21CCNCC2 WYZZNMWIWHRXRM-UHFFFAOYSA-N 0.000 claims 2
- XKEYAOJRNJYJMM-UHFFFAOYSA-N 3,6-diazabicyclo[3.2.0]heptane Chemical compound C1NCC2CNC21 XKEYAOJRNJYJMM-UHFFFAOYSA-N 0.000 claims 2
- GHUJOZDTTMAMKK-UHFFFAOYSA-N 3,8-diazatricyclo[5.2.1.01,5]decane Chemical compound C123CNCC1CC(NC2)C3 GHUJOZDTTMAMKK-UHFFFAOYSA-N 0.000 claims 2
- WROMFHICINADER-UHFFFAOYSA-N 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine Chemical group C1NCCN2C=NC=C21 WROMFHICINADER-UHFFFAOYSA-N 0.000 claims 2
- 229910003827 NRaRb Inorganic materials 0.000 claims 2
- 241000589516 Pseudomonas Species 0.000 claims 2
- UMIZTIYZNFUATK-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b][1,4]oxazine Chemical compound O1CCNC2CNCC21 UMIZTIYZNFUATK-UHFFFAOYSA-N 0.000 claims 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims 1
- NRPURYORSRHBCU-UHFFFAOYSA-N 5-oxa-2-azaspiro[3.4]octane Chemical group C1NCC11OCCC1 NRPURYORSRHBCU-UHFFFAOYSA-N 0.000 claims 1
- 101000742087 Bacillus subtilis (strain 168) ATP-dependent threonine adenylase Proteins 0.000 claims 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims 1
- 102100038916 Caspase-5 Human genes 0.000 claims 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 claims 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 claims 1
- 101000744152 Naja oxiana Cytotoxin 2 Proteins 0.000 claims 1
- 101000774739 Thermus thermophilus Aspartokinase Proteins 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 210000005056 cell body Anatomy 0.000 claims 1
- LFVPBERIVUNMGV-UHFFFAOYSA-N fasudil hydrochloride Chemical compound Cl.C=1C=CC2=CN=CC=C2C=1S(=O)(=O)N1CCCNCC1 LFVPBERIVUNMGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 64
- 238000002360 preparation method Methods 0.000 abstract description 55
- 208000015181 infectious disease Diseases 0.000 abstract description 16
- 239000003795 chemical substances by application Substances 0.000 abstract description 15
- 238000011282 treatment Methods 0.000 abstract description 12
- 229940079593 drug Drugs 0.000 abstract description 10
- 230000008569 process Effects 0.000 abstract description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract description 2
- 241000233855 Orchidaceae Species 0.000 abstract 6
- 244000128206 Pyracantha coccinea Species 0.000 abstract 1
- 235000003105 Pyracantha coccinea Nutrition 0.000 abstract 1
- 230000008520 organization Effects 0.000 abstract 1
- 102220240796 rs553605556 Human genes 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 150
- 238000005481 NMR spectroscopy Methods 0.000 description 124
- 238000004128 high performance liquid chromatography Methods 0.000 description 116
- 239000011541 reaction mixture Substances 0.000 description 94
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 80
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 73
- 239000002253 acid Substances 0.000 description 71
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 68
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 61
- 239000012044 organic layer Substances 0.000 description 61
- 239000000243 solution Substances 0.000 description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 49
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 description 46
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 43
- 229940093499 ethyl acetate Drugs 0.000 description 41
- 235000019439 ethyl acetate Nutrition 0.000 description 41
- 239000000047 product Substances 0.000 description 40
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 38
- 125000001841 imino group Chemical group [H]N=* 0.000 description 36
- 229910052938 sodium sulfate Inorganic materials 0.000 description 32
- 235000011152 sodium sulphate Nutrition 0.000 description 32
- 239000012267 brine Substances 0.000 description 31
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000007787 solid Substances 0.000 description 30
- 238000004440 column chromatography Methods 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- 238000001035 drying Methods 0.000 description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
- 125000005842 heteroatom Chemical group 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- 239000012299 nitrogen atmosphere Substances 0.000 description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- 229960002260 meropenem Drugs 0.000 description 14
- 230000001580 bacterial effect Effects 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical class OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 11
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- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1
- 230000003519 ventilatory effect Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 239000008760 zaizhang I Substances 0.000 description 1
- KGPGQDLTDHGEGT-JCIKCJKQSA-N zeven Chemical compound C=1C([C@@H]2C(=O)N[C@H](C(N[C@H](C3=CC(O)=C4)C(=O)NCCCN(C)C)=O)[C@H](O)C5=CC=C(C(=C5)Cl)OC=5C=C6C=C(C=5O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@H](O5)C(O)=O)NC(=O)CCCCCCCCC(C)C)OC5=CC=C(C=C5)C[C@@H]5C(=O)N[C@H](C(N[C@H]6C(=O)N2)=O)C=2C(Cl)=C(O)C=C(C=2)OC=2C(O)=CC=C(C=2)[C@H](C(N5)=O)NC)=CC=C(O)C=1C3=C4O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O KGPGQDLTDHGEGT-JCIKCJKQSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
La présente invention concerne des composés de carbapénème, leurs stéréoisomères, et leurs sels ou N-oxydes pharmaceutiquement acceptables, qui peuvent être utiles pour traiter les infections bactériennes, en particulier les infections bactériennes pharmacorésistantes, ainsi que des procédés de préparation des composés, des compositions pharmaceutiques de ces composés et leur utilisation dans le traitement d'une infection bactérienne.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN201641009127 | 2016-03-16 | ||
IN201641009127 | 2016-03-16 | ||
PCT/IN2017/000060 WO2017158616A1 (fr) | 2016-03-16 | 2017-03-15 | Composés de carbapénème |
Publications (2)
Publication Number | Publication Date |
---|---|
CA3015309A1 CA3015309A1 (fr) | 2017-09-21 |
CA3015309C true CA3015309C (fr) | 2024-02-13 |
Family
ID=58715155
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA3015309A Active CA3015309C (fr) | 2016-03-16 | 2017-03-15 | Composes de carbapeneme |
Country Status (13)
Country | Link |
---|---|
US (1) | US11180504B2 (fr) |
EP (1) | EP3430013B1 (fr) |
JP (1) | JP7213173B2 (fr) |
KR (1) | KR102435777B1 (fr) |
CN (1) | CN109415365B (fr) |
AU (1) | AU2017235293B2 (fr) |
BR (1) | BR112018068462A2 (fr) |
CA (1) | CA3015309C (fr) |
IL (1) | IL261782B1 (fr) |
MA (1) | MA43791A (fr) |
MX (1) | MX2018011095A (fr) |
WO (1) | WO2017158616A1 (fr) |
ZA (1) | ZA201805158B (fr) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020027553A1 (fr) * | 2018-08-03 | 2020-02-06 | 한양대학교 에리카산학협력단 | Sonde pour la détection de bactéries résistantes au carbapénème et utilisation correspondante |
WO2023007325A1 (fr) * | 2021-07-28 | 2023-02-02 | University Of Kwazulu-Natal | INHIBITEURS DE MÉTALLO-β-LACTAMASES |
WO2023243601A1 (fr) * | 2022-06-13 | 2023-12-21 | モジュラス株式会社 | Composé d'amine cyclique d'azacycloalkyle carbonyle |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4194047A (en) | 1975-11-21 | 1980-03-18 | Merck & Co., Inc. | Substituted N-methylene derivatives of thienamycin |
EP0017992A1 (fr) | 1979-04-19 | 1980-10-29 | Merck & Co. Inc. | Acides 1-carbadéthiapén-2-èm-carboxyliques substitués en position 2 et 6, procédés pour les préparer, compositions pharmaceutiques antibiotiques les contenant et procédé pour préparer des intermédiaires |
EP0044170A1 (fr) | 1980-07-11 | 1982-01-20 | Beecham Group Plc | Antibiotiques bêta-lactame, leur préparation et leur utilisation |
EP0059554A3 (fr) | 1981-02-27 | 1982-10-20 | Beecham Group Plc | Antibiotiques bêta-lactame, un procédé pour leur préparation et leur application en compositions pharmaceutiques |
JPS57158785A (en) | 1981-02-27 | 1982-09-30 | Beecham Group Ltd | Beta-lactam antibiotic, manufacture and medicinal composition |
CA1283906C (fr) | 1983-05-09 | 1991-05-07 | Makoto Sunagawa | COMPOSE DE .beta.-LACTAM ET PROCEDE DE PRODUCTION |
JPS60233076A (ja) * | 1984-05-03 | 1985-11-19 | Sumitomo Chem Co Ltd | 新規なβ−ラクタム化合物およびその製造法 |
JPS6383062A (ja) * | 1986-09-26 | 1988-04-13 | Nippon Redarii Kk | アゼチジンスルホン酸誘導体 |
CA2004798A1 (fr) * | 1988-12-09 | 1990-06-09 | Jacques Banville | 6-aminoalkyl carbapenemes |
JPH04211083A (ja) * | 1990-02-23 | 1992-08-03 | Sankyo Co Ltd | カルバペネム−3−カルボン酸誘導体 |
JP2934283B2 (ja) * | 1990-05-29 | 1999-08-16 | 第一製薬株式会社 | カルバペネム誘導体 |
JP2559949B2 (ja) | 1991-06-04 | 1996-12-04 | 三共株式会社 | 1−メチルカルバペネム誘導体 |
US5317016A (en) | 1991-08-20 | 1994-05-31 | Shionogi Seiyaku Kabushiki Kaisha | Pyrrolidylthiocarbapenem derivative |
GB9202298D0 (en) * | 1992-02-04 | 1992-03-18 | Ici Plc | Antibiotic compounds |
JP3411589B2 (ja) * | 1992-05-11 | 2003-06-03 | 第一製薬株式会社 | カルバペネム誘導体 |
US5602118A (en) | 1993-03-16 | 1997-02-11 | American Cyanamid Company | 2-thiosubstituted carbapenems |
JP3199300B2 (ja) | 1994-05-09 | 2001-08-13 | 三共株式会社 | 1−メチルカルバペネム誘導体 |
-
2017
- 2017-03-15 WO PCT/IN2017/000060 patent/WO2017158616A1/fr active Application Filing
- 2017-03-15 JP JP2019500051A patent/JP7213173B2/ja active Active
- 2017-03-15 US US16/083,980 patent/US11180504B2/en active Active
- 2017-03-15 MX MX2018011095A patent/MX2018011095A/es unknown
- 2017-03-15 KR KR1020187029573A patent/KR102435777B1/ko active IP Right Grant
- 2017-03-15 AU AU2017235293A patent/AU2017235293B2/en active Active
- 2017-03-15 EP EP17724297.1A patent/EP3430013B1/fr active Active
- 2017-03-15 BR BR112018068462A patent/BR112018068462A2/pt active Search and Examination
- 2017-03-15 CA CA3015309A patent/CA3015309C/fr active Active
- 2017-03-15 MA MA043791A patent/MA43791A/fr unknown
- 2017-03-15 IL IL261782A patent/IL261782B1/en unknown
- 2017-03-15 CN CN201780017093.0A patent/CN109415365B/zh active Active
-
2018
- 2018-07-31 ZA ZA2018/05158A patent/ZA201805158B/en unknown
Also Published As
Publication number | Publication date |
---|---|
AU2017235293B2 (en) | 2021-02-04 |
ZA201805158B (en) | 2023-01-25 |
JP7213173B2 (ja) | 2023-01-26 |
KR102435777B1 (ko) | 2022-08-23 |
AU2017235293A1 (en) | 2018-08-23 |
CN109415365A (zh) | 2019-03-01 |
KR20180133420A (ko) | 2018-12-14 |
WO2017158616A1 (fr) | 2017-09-21 |
EP3430013B1 (fr) | 2023-11-15 |
CN109415365B (zh) | 2022-08-09 |
BR112018068462A2 (pt) | 2019-01-22 |
MX2018011095A (es) | 2019-01-10 |
EP3430013A1 (fr) | 2019-01-23 |
MA43791A (fr) | 2018-11-28 |
WO2017158616A8 (fr) | 2018-06-07 |
JP2019512547A (ja) | 2019-05-16 |
RU2018136064A (ru) | 2020-04-16 |
IL261782A (en) | 2018-10-31 |
CA3015309A1 (fr) | 2017-09-21 |
RU2018136064A3 (fr) | 2020-04-16 |
US20200291029A1 (en) | 2020-09-17 |
IL261782B1 (en) | 2024-03-01 |
US11180504B2 (en) | 2021-11-23 |
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